Claims for Patent: 6,878,698

Claims for Patent: 6,878,698

Title:

Anti-inflammatory androstane derivatives

Abstract:

According to one aspect of the invention, there is provided a pharmaceutical formulation for administration by inhalation comprising a compound of formula (I), ##STR1## wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and {character pullout} represents a single or a double bond; and salts and solvates thereof together with a long-acting .beta..sub.2 -adrenoreceptor agonist which formulation has a therapeutically useful effect in the treatment of COPD over a period of 24 hours or more.

1. A method of treatment of COPD comprising the administration by inhalation of a pharmaceutical formulation comprising a compound of formula (I), ##STR32## wherein R.sub.1
represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are
the same or different and each represents hydrogen or halogen; and {character pullout} represents a single or a double bond; or a salt or solvate thereof, together with a long-acting .beta..sub.2 -adrenoreceptor agonist wherein said formulation has a
therapeutically useful effect in the treatment of COPD over a period of 24 hours or more.

2. The method of treatment claim 1, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

3. The method of treatment claim 2, wherein said pharmaceutical formulation further comprising a particulate carrier.

4. The method treatment of claim 3, wherein the carrier in said pharmaceutical formulation is lactose.

5. The method of treatment of claim 1, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

6. The method of treatment of claim 2, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

7. A method of treatment of COPD over a period of 24 hours, or more, comprising delivering to a patient one or more doses once-per-day from an inhaler containing a plurality of doses of a pharmaceutical formulation comprising a compound of
formula (I) ##STR33## wherein R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration)
or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and {character pullout} represents a single or a double bond; or a salt or solvate thereof, together with a long-acting .beta..sub.2 -adrenoreceptor
agonist which formulation has a therapeutically useful effect in the treatment of COPD over a period of 24 hours or more, and which doses are suitable for once-per-day administration of the formulation by inhalation.

8. The method of treatment of claim 7, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

9. The method of treatment of claim 8, wherein the formulation further comprises a particulate carrier.

10. The method of treatment of claim 9, wherein the carrier is lactose.

11. The method of treatment of claim 7, wherein the formulation further comprises a liquefied propellant gas.

12. The method of treatment of claim 8, wherein the formulation further comprises a liquefied propellant gas.

13. A method of treatment of COPD by inhalation comprising administering by once-per-day dosing from an inhaler containig a plurality of doses of a pharmaceutical formulation comprising a particulate compound of formula (I) ##STR34## wherein
R.sub.1 represents C.sub.1-6 alkyl or C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and
R.sub.5 are the same or different and each represents hydrogen or halogen; and {character pullout} represents a single or a double bond; or a salt or solvate thereof, together with a long-acting .beta..sub.2 -adrenoreceptor, a particulate long-acting
.beta..sub.2 -adrenoreceptor agonist and a carrier each drug being present in an amount adequate to provide a therapeutically useful effect in the treatment of COPD over a period of 24 hours or more following once-per-day dosing by inhalation.

14. The method of treatment of claim 1, wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

15. The method of treatment of claim 2 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

16. The method of treatment of claim 3 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

17. The method of treatment of claim 4 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

18. The method of treatment of claim 5 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

19. The method of treatment of claim 6 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

20. The method of treatment of claim 7 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

21. The method of treatment of claim 8 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

22. The method of treatment of claim 9 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

23. The method of treatment of claim 10 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

24. The method of treatment of claim 11 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

25. The method of treatment of claim 12 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.alpha.-[(4 -methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carb othioic acid
S-fluoromethyl ester or a salt or solvate thereof.

26. The method of treatment of claim 13 wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-11.beta.-hydroxy-16.alpha.-methyl-17.beta.-[(4- methyl-1,3-thiazole-5-carbonyl)oxy]-3-oxo-androsta-1,4-diene-17.beta.-carbo thioic acid
S-fluoromethyl ester or a salt or solvate thereof.

27. The method of treatment of claim 1, in which R.sub.1 represents fluoromethyl, chloromethyl, bromomethyl or 2'-fluoroethyl.

28. The method of treatment of claim 27, in which R.sub.1 represents fluoromethyl.

29. The method of treatment of claim 1, in which R.sub.2 represents --C(.dbd.O)-heteroaryl.

30. The method of treatment of claim 29, wherein heteroaryl represents a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms selected from O, N and S which may optionally be substituted.

31. The method of treatment of claim 30, wherein the heterocyclic ring is substituted with one or more substituents selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy and halogen.

32. The method of treatment of claim 30, in which the heterocyclic ring is furanyl, pyrrolyl or thiophenyl.

33. The method of treatment of claim 32, in which the heterocyclic ring is furanyl or thiophenyl.

34. The method of treatment of claim 30, in which the 5-membered heterocyclic ring contains 2 heteroatoms selected from O, N and S.

35. The method of treatment of claim 24, wherein the heterocyclic ring is selected from thiazolyl, isothiazolyl, pyrazolyl and imidazolyl.

36. The method of treatment of claim 30, in which the 5-membered heterocyclic ring contains 3 heteroatoms selected from O, N and S.

37. The method of treatment of claim 36, wherein the heterocycle is thiadiazolyl.

38. The method of treatment of claim 32, wherein the heterocyclic ring is substituted with one or more substituents selected from C.sub.1-6 alkyl and halogen.

39. The method of treatment of claim 1, in which R.sub.3 is methyl.

40. The method of treatment of claim 1, in which R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

41. The method of treatment of claim 1, in which R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

42. The method of treatment of claim 1, in which both R.sub.4 and R.sub.5 are fluorine.

43. The method of treatment of claim 1, in which R.sub.1 is fluoromethyl; R.sub.2 is --C(.dbd.O)-2-furanyl; R.sub.3 is methyl; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine; and {character pullout}
represents a single or a double bond.

44. The method of treatment of claim 43, in which R.sub.4 and R.sub.5 are each fluorine.

45. The method of treatment of claim 1, in which {character pullout} represents a double bond.

48. The method of treatment of claim 1, wherein the method is for veterinary medicine.

49. The method of treatment of claim 1, wherein the method is for human medicine.

50. The method of treatment of claim 1, wherein the compound of formula (I) or a salt or solvate thereof is together, if desirable, in admixture with one or more physiologically acceptable diluents or carriers.

51. The method of treatment of claim 1, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and or a cosolvent.

52. The method of treatment of claim 1, wherein in the compound of formula (I), R.sub.1 represents C.sub.1-6 alkyl; R.sub.2 represents --C(.dbd.O)-aryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta.
configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen, and {character pullout} represents a single or a double bond; or salts and solvates thereof.

53. The method of treatment of claim 52, wherein in the compound of formula (I), R.sub.3 represents methyl (which may be in either the .alpha. or .beta. configuration); R.sub.4 and R.sub.5 are the same or different and each represents
halogen; and {character pullout} represents a single or a double bond; or salts and solvates thereof.

54. The method of treatment of claim 52, wherein R.sub.3 is methyl.

55. The method of treatment of claim 52, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

56. The method of treatment of claim 52, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

57. The method of treatment of claim 52, wherein both R.sub.4 and R.sub.5 are fluorine.

59. The method of treatment of claim 52, wherein the method is for veterinary medicine.

60. The method of treatment of claim 52, wherein the method is for human medicine.

61. The method of treatment of claim 52, wherein the compound of formula (I) or a salt or solvate thereof is together, if desirable, in admixture with one or more physiologically acceptable diluents or carriers.

62. The method of treatment of claim 52, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and/or a cosolvent.

63. The method of treatment of claim 61, wherein the composition is a dry powder or spray.

64. The method of treatment of claim 63, wherein the composition is a dry powder.

65. The method of treatment of claim 63, wherein the composition is a spray.

66. The method of treatment of claim 1, wherein the .beta..sub.2 -adrenoreceptor agonist is at least one selected from the group consisting of salmeterol, salbutamol, formoterol, salmefamol, fenoterol, terbutaline and salts thereof.

67. The method of treatment of claim 52, wherein the .beta..sub.2 -adrenoreceptor agonist is at least one selected from the group consisting of salmeterol, salbutamol, formoterol, salmefamol, fenoterol, terbutaline and salts thereof.

68. The method of treatment of claim 1, wherein said compound of formula (I) has a particle size in the range of 1-10 .mu.m.

69. The method of treatment of claim 52, wherein said compound of formula (I) has a particle size in the range of 1-10 .mu.m.

70. The method of treatment of claim 52, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

71. The method of treatment of claim 70, wherein said pharmaceutical formulation further comprising a particulate carrier.

72. The method of treatment of claim 71, wherein the carrier in said pharmaceutical formulation is lactose.

73. The method of treatment of claim 52, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

74. The method of treatment of claim 70, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

75. The method of treatment of claim 1, wherein R.sub.1 represents C.sub.1-6 haloalkyl; R.sub.2 represents --C(.dbd.O)-heteroaryl; R.sub.3 represents hydrogen, methyl (which may be in either the .alpha. or .beta. configuration) or methylene; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or halogen; and {character pullout} represents a single or a double bond; or salts and solvates thereof.

76. The method of treatment of claim 75, wherein R.sub.3 represents methyl (which may be in either the .alpha. or .beta. configuration); R.sub.4 and R.sub.5 are the same or different and each represents halogen; and {character pullout}
represents a single or a double bond; or salts and solvates thereof.

79. The method of treatment of claim 75, wherein the heteroaryl of R.sub.2 represents a 5-membered heterocyclic aromatic ring containing 1 to 3 heteroatoms and each of said 1-3 heteroatoms is independently selected from the group consisting of
O, N and S which may optionlly be substituted.

80. The method of treatment of claim 79, wherein the 5-membered heterocyclic aromatic ring is substituted with one or more substituents selected from the group consisting of C.sub.1-6 alkyl, C.sub.1-6 alkoxy and halogen.

81. The method of treatment of claim 80, wherein the 5-membered heterocylic aromatic ring is selected from the group consisting of furanyl, pyrrolyl and thiophenyl.

82. The method of treatment of claim 81, wherein the 5-membered heterocyclic ring is furanyl or thiophenyl.

83. The method of treatment of claim 79, wherein the 5-membered heterocyclic ring contains 2 heteroatoms and each of said 2 heteroatoms is independently selected from the group cousisting of O, N and S.

84. The method of treatment of claim 79, wherein the 5-membered heterocyclic ring is selected from the group consisting of thiazolyl, isothiazolyl, pyrazolyl and imidazolyl.

85. The method of treatment of claim 79, wherein the 5-membered heterocycic ring contains 3 heteroatoms and each of said 3 heteroatoms is independently selected from the group consisting of O, N and S.

86. The method of treatment of claim 79, wherein the heterocycle of the 5-membered heterocyclic ring is thiadiazolyl.

87. The method of treatment of claim 79, wherein the 5-membered heterocyclic ring is substituted with one or more substituents selected from the group consisting of C.sub.1-6 alkyl and halogen.

88. The method of treatment of claim 75, wherein R.sub.3 is methyl.

89. The method of treatment of claim 75, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen, fluorine or chlorine.

90. The method of treatment of claim 75, wherein R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine.

91. The method of treatment of claim 75, wherein both R.sub.4 and R.sub.5 are fluorine.

92. The method of treatment of claim 75, wherein R.sub.1 is fluoromethyl; R.sub.2 is --C(.dbd.O)-2-furanyl; R.sub.3 is methyl; R.sub.4 and R.sub.5 are the same or different and each represents hydrogen or fluorine; and {character pullout}
represents a single or a double bond.

94. The method of treatment of claim 75, wherein the method is for veterinary medicine.

95. The method of treatment of claim 75, wherein the method is for human medicine.

96. The method of treatment of claim 75, wherein the pharmaceutical composition is in admixture with one or more physiologically acceptable diluents or carriers.

97. The method of treatment of claim 75, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and/or a cosolvent.

98. The method of treatment of claim 96, wherein the composition is a dry powder or spray.

99. The method of treatment of claim 98, wherein the composition is a dry powder.

100. The method of treatment of claim 98, wherein the composition is a spray.

101. The method of treatment of claim 75, wherein the .beta..sub.2 -adrenoreceptor agonist is at least one selected from the group consisting of salmeterol, salbutamol, formoterol, salmefamol, fenoterol, terbutaline and salts thereof.

102. The method of treatment of claim 75, wherein said compound of formula (I) has a particle size in the range of 1-10 .mu.m.

103. The method of treatment of claim 75, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

104. The method of treatment of claim 103, wherein said pharmaceutical formulation further comprising a particulate carrier.

105. The method of treatment of claim 104, wherein the carrier in said pharmaceutical formulation is lactose.

106. The method of treatment of claim 75, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

108. The method of treatment of claim 1, wherein the compound of formula (I) is 6.alpha.,9.alpha.-Difluoro-17.alpha.-[(2-furanylcarbonyl)oxy]-11.beta.-hyd roxy-16.alpha.-methyl-3-oxo-androsta-1,4-diene-17.beta.-carbothioic acid S-fluoromethyl
ester or a salt or solvate thereof.

109. The method of treatment of claim 108, wherein the compound or salt or solvate thereof is together, if desirable, in admixture with one or more physiologically acceptable diluents or carriers.

110. The method of treatment of claim 108, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and/or a cosolvent.

111. The method of treatment of claim 108, wherein the pharmaceutical formulation is a dry powder or spray.

112. The method of treatment of claim 111, wherein the composition is a dry powder.

113. The method of treatment of claim 111, wherein the composition is a spray.

114. The method of treatment of claim 108, wherein the .beta..sub.2 -adrenoreceptor agonist is at least one selected from the group consisting of salmeterol, salbutamol, formoterol, salmefamol, fenoterol, terbutaline and salts thereof.

115. The method of treatment of claim 108, wherein said compound of formula (I) has a particle size in the range of 1-10 .mu.m.

116. The method of treatment of claim 108, wherein the method is for veterinary medicine.

117. The method of treatment of claim 108, wherein the method is for human medicine.

118. The method of treatment of claim 108, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

119. The method of treatment of claim 118, wherein said pharmaceutical formulation further comprising a particulate carrier.

120. The method of treatment of claim 119, wherein the carrier in said pharmaceutical formulation is lactose.

121. The method of treatment of claim 108, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

122. The method of treatment of claim 118, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

123. The method of treatment of claim 14, wherein the compound or salt or solvate thereof is together, if desirable, in admixture with one or more physiologically acceptable diluents or carriers.

124. The method of treatment of claim 14, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and/or a cosolvent.

125. The method of treatment of claim 14, wherein the pharmaceutical formulation is a dry powder or spray.

126. The method of treatment of claim 125, wherein the pharmaceutical formulation is a dry powder.

127. The method of treatment of claim 125, wherein the composition is a spray.

128. The method of treatment of claim 14, wherein the .beta..sub.2 -adrenoreceptor agonist is at least one selected from the group consisting of salmeterol, salbutamol, formoterol, salmefamol, fenoterol, terbutaline and salts thereof.

129. The method of treatment of claim 14, wherein said compound of formula (I) has a particle size in the range of 1-10 .mu.m.

130. The method of treatment of claim 14, wherein the method is for veterinary medicine.

131. The method of treatment of claim 14, wherein the method is for human medicine.

132. The method of treatment of claim 14, wherein the compound of formula (I) or a solvate thereof and the long-acting .beta..sub.2 -adrenoreceptor agonist are both present in particulate form.

133. The method of treatment of claim 132, wherein said pharmaceutical formulation further comprising a particulate carrier.

134. The method of treatment of claim 133, wherein the carrier in said pharmaceutical formulation is lactose.

135. The method of treatment of claim 14, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

136. The method of treatment of claim 132, wherein said pharmaceutical formulation further comprises a liquified propellant gas.

137. The method of treatment of claim 14, wherein the compound or salt or solvate thereof is together, if desirable, in admixture with one or more physiologically acceptable diluents or carriers.

138. The method of treatment of claim 14, wherein the pharmaceutical formulation further comprises a fluorocarbon or hydrogen-containing chlorofluoro carbon as propellant, optionally in combination with a surfactant and/or a cosolvent.

139. The method of treatment of claim 14, wherein the pharmaceutical formulation is a dry powder or spray.

140. The method of treatment of claim 139, wherein the pharmaceutical formulation is a dry powder.

141. The method of treatment of claim 139, wherein the composition is a spray.

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